At the time of Prohibition, Key West must have looked something like a tropical West Egg. With beer and rum smuggled from Cuba and whiskey, rye, and scotch from the British Isles through Nassau, the island was a free-for-all where violence lived with opulence, rules were bent, money was made, and the smell of cigars lingered in the air. Key West was far from the picturesque island we see today—a synonym for tranquility and lazy afternoons on the beach. But in many ways, the memory of times gone by remains on the island, whispering its mysteries to those who care to listen, to those staying at the Gates Hotel Key West.
The Gates, as the name implies, welcomes its visitors at the entry way to Florida’s southernmost island. Upon first glance, the hotel looks like a boutique with its neutral tones, crisp geometry, and minimalist style. The guest rooms—ranging from the Standard to the Lifestyle to the Scene—reinforce this ambiance with their creamy white walls, airy spaces, and nautical motifs. Custom platform pine beds and Bali-imported wood tables add an organic touch, while regional lore is present in photography by local Jorge de la Torriente and a selection of Key West-inspired books.
But a look beyond the façade reveals otherwise. Just walk to Rum Row—the Gates’ contemporary pool bar—and you’ll learn that the name refers to the line of liquor-carrying ships anchored near U.S. ports that supplied the illegal alcohol trade during Prohibition. Take a look at the cocktail menu. Ironically, you’ll find First Legal Rum from no other than Key West First Legal Rum Distillery, yet another hint at the mayhem that used to dictate a way of life here.
Try the Up in Smoke, a tribute to the cigar industry, which features First Legal’s Aged Raw and Unfiltered Rum or the Tomoka Mojito, which bears the name of bootlegger William McCoy’s famous ship. Or, maybe you’re a sit-and-sip kind of person who would prefer a neat aged rum. The bartenders at Rum Row can set you up with that too.
While at Rum Row, make a stop at the Blind Pig—the Gate’s signature food truck that offers delicious tapas-style “conch fusion”: fusion of Bahamian, Caribbean, Cuban, and Floridian flavors. You’ll find a constantly-rotating menu with items like the Flapper in a Wrapper (grilled chicken wrap on a whole wheat tortilla with wild berry mint vinaigrette, arugula, crushed apples, and herb feta), Right in the Kisser (half pound angus burger on brioche roll with optional toppings), ceviche, fish tacos, and flatbread “a la Plancha.”
A good meal and live music go hand in hand, so make sure to grab a seat on Rum Row’s pool deck Wednesday to Sunday where acoustic guitar soloists and bands perform for your listening pleasure. Then again, private poolside cabanas, with their option of VIP bottle service, can make for a decadent evening.
And lastly, a stay at the Gates Hotel is not complete without a visit to the Cigar Garden where guests can purchase and enjoy cigars from Rodriguez Cigar Factory, the oldest operating cigar manufacturer in Key West. The cigars are hand-rolled and contain cured, aged vintage tobacco leaves in the traditional Cuban style. They remind us of yet another way history—the first cigar was made in Key West in 1831—continues to live in the present.
Before you leave the island, we recommend a water sport activity—whether it’s snorkeling, deep-sea fishing, or catamaran sailing—organized through the Gates’ concierge services or a visit to Key West’s top destinations outside the hotel—Duval Street, the Southernmost Point Buoy, or the Ernest Hemingway Home.
And while you’re looking out over the sea, at the place where countless others have stood before you, perhaps you too will get the sensation of being “borne ceaselessly into the past.”
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